EP0467708A2 - Schutz gegen Mikroorganismen auf Pflanzen mit 1-Hydroxymethylpyrazolen - Google Patents

Schutz gegen Mikroorganismen auf Pflanzen mit 1-Hydroxymethylpyrazolen Download PDF

Info

Publication number: EP0467708A2
Authority: EP; European Patent Office
Prior art keywords: plant; composition; compound; seed; formula
Prior art date: 1990-07-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

EP91306611A

Other languages

English (en)

French (fr)

Other versions

EP0467708B1 (de

EP0467708A3 (en

Inventor

Miguel L. Pulido

Joseph G. Fenyes

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Buckman Laboratories International Inc

Original Assignee

Buckman Laboratories International Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-07-20

Filing date

1991-07-19

Publication date

1992-01-22

1991-07-19 Application filed by Buckman Laboratories International Inc filed Critical Buckman Laboratories International Inc

1992-01-22 Publication of EP0467708A2 publication Critical patent/EP0467708A2/de

1992-08-19 Publication of EP0467708A3 publication Critical patent/EP0467708A3/en

1998-11-04 Application granted granted Critical

1998-11-04 Publication of EP0467708B1 publication Critical patent/EP0467708B1/de

2011-07-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

244000005700 microbiome Species 0.000 title claims abstract description 21
BYUMAPPWWKNLNX-UHFFFAOYSA-N pyrazol-1-ylmethanol Chemical class OCN1C=CC=N1 BYUMAPPWWKNLNX-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 38
239000000203 mixture Substances 0.000 claims abstract description 29
238000000034 method Methods 0.000 claims abstract description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 6
235000013311 vegetables Nutrition 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
229910052794 bromium Inorganic materials 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
235000013339 cereals Nutrition 0.000 claims abstract description 4
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
244000038559 crop plants Species 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
229910052740 iodine Inorganic materials 0.000 claims abstract 2
241000233866 Fungi Species 0.000 claims description 13
241000894006 Bacteria Species 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
230000000855 fungicidal effect Effects 0.000 claims description 10
230000000844 anti-bacterial effect Effects 0.000 claims description 9
238000005507 spraying Methods 0.000 claims description 8
OBENDWOJIFFDLZ-UHFFFAOYSA-N (3,5-dimethylpyrazol-1-yl)methanol Chemical compound CC=1C=C(C)N(CO)N=1 OBENDWOJIFFDLZ-UHFFFAOYSA-N 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
239000000843 powder Substances 0.000 claims description 6
241000589774 Pseudomonas sp. Species 0.000 claims description 5
230000035755 proliferation Effects 0.000 claims description 5
241000549404 Hyaloperonospora parasitica Species 0.000 claims description 4
241000588701 Pectobacterium carotovorum Species 0.000 claims description 4
239000003899 bactericide agent Substances 0.000 claims description 4
235000013399 edible fruits Nutrition 0.000 claims description 4
239000000417 fungicide Substances 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
241000190150 Bipolaris sorokiniana Species 0.000 claims description 3
241000588724 Escherichia coli Species 0.000 claims description 3
241000223221 Fusarium oxysporum Species 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
241001518731 Monilinia fructicola Species 0.000 claims description 3
241000589517 Pseudomonas aeruginosa Species 0.000 claims description 3
241000918584 Pythium ultimum Species 0.000 claims description 3
241000191967 Staphylococcus aureus Species 0.000 claims description 3
241001148118 Xanthomonas sp. Species 0.000 claims description 3
239000006185 dispersion Substances 0.000 claims description 3
239000000945 filler Substances 0.000 claims description 3
230000009969 flowable effect Effects 0.000 claims description 3
239000000575 pesticide Substances 0.000 claims description 3
239000003381 stabilizer Substances 0.000 claims description 3
239000000080 wetting agent Substances 0.000 claims description 3
241000213004 Alternaria solani Species 0.000 claims description 2
241000813090 Rhizoctonia solani Species 0.000 claims description 2
241000196324 Embryophyta Species 0.000 description 21
239000000243 solution Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
240000003259 Brassica oleracea var. botrytis Species 0.000 description 7
241000233855 Orchidaceae Species 0.000 description 6
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 6
230000035784 germination Effects 0.000 description 6
150000003217 pyrazoles Chemical class 0.000 description 6
235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 5
231100000674 Phytotoxicity Toxicity 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
230000001580 bacterial effect Effects 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
239000008272 agar Substances 0.000 description 3
230000000845 anti-microbial effect Effects 0.000 description 3
230000007226 seed germination Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
241000588698 Erwinia Species 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000008223 sterile water Substances 0.000 description 2
DLGMQZRYWBFVKO-UHFFFAOYSA-N (3,5-dimethylpyrazol-1-yl)methanol;hydrochloride Chemical compound Cl.CC=1C=C(C)N(CO)N=1 DLGMQZRYWBFVKO-UHFFFAOYSA-N 0.000 description 1
CABHXTNYNGUYFF-UHFFFAOYSA-N 1-(1h-pyrazol-5-yl)ethanol Chemical class CC(O)C1=CC=NN1 CABHXTNYNGUYFF-UHFFFAOYSA-N 0.000 description 1
-1 3,5-dimethyl-4-substituted-1-hydroxymethylpyrazoles Chemical class 0.000 description 1
241000228257 Aspergillus sp. Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
240000007124 Brassica oleracea Species 0.000 description 1
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
241000421360 Breynia disticha Species 0.000 description 1
241001214984 Crinum thaianum Species 0.000 description 1
241001523681 Dendrobium Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
241000446313 Lamella Species 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 description 1
241000190074 Oncidium Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
241001223281 Peronospora Species 0.000 description 1
240000001987 Pyrus communis Species 0.000 description 1
235000014443 Pyrus communis Nutrition 0.000 description 1
241000109329 Rosa xanthina Species 0.000 description 1
235000004789 Rosa xanthina Nutrition 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
240000003768 Solanum lycopersicum Species 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012677 causal agent Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
229940124561 microbicide Drugs 0.000 description 1
239000002855 microbicide agent Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000001965 potato dextrose agar Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
241000894007 species Species 0.000 description 1
230000004763 spore germination Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

the subject of the present invention is directed to a method and composition for the control of microorganisms on plants. More particularly, the present invention relates to the use of certain 1-hydroxyethylpyrazoles as an agricultural microbicide, especially as a bactericide or fungicide.
the present invention provides a method for the control of microorganisms, including but not limited to bacteria and fungi, comprising the step of applying to a plant or the seed thereof an amount sufficient to inhibit the growth and proliferation of at least one microorganism on the plant or seed of a compound having the formula I wherein R and R' are independently hydrogen or alkyl of 1 to 4 carbon atoms, and R" is (a) hydrogen, (b) a halogen atom F, Cl, Br or or (c) a nitro group, or a salt of said compound.
Salts of the compounds of the invention include the hydrobromide, hydroiodide, phosphate and sulphate salts, preferably the hydrochloride salts.
the application step may be accomplished by spraying with a composition comprising a compound of formula I.
a sufficient amount of the compound of the formula can be in the range of about 2,500 to about 30,000 ppm of the composition, preferably in the range of about 15,000 to about 25,000 ppm of the composition.
the compound of formula can be 3,5-dimethyl-1-hydroxymethylpyrazole or3,5-dimethyl-1-hydroxymethylpyrazole hydrochloride.
the microorganisms can be bacteria or fungi.
the bacteria can be Erwinia caratovora, Agrobacteria sp., corynebacteria, Xanthomonas sp., Pseudomonas sp., Escherichia coli, Staphylococcus aureus or Pseudomonas aeruginosa.
the fungi can be Pythium ultimum, Helminthosporium sativum, Rhizoctonia solani, Monilia fructicola, Fusarium oxysporum, Peronospora parasitica or Alternaria solani.
the plant or seed can be ornamental plants, fruit plants, vegetable plants, cereal crop plants and seeds thereof.
the application of the compound or hydrochloride salt to the plant or seed can be done two or more times.
a composition which comprises an amount per unit weight of the compound of formula I sufficient to inhibit the growth and proliferation of at least one microorganism on the plant, together with an inert carrier.
the compound can be 3,5-dimethyl-1-hydroxymethylpyrazole or 3,5-dimethyl-1-hydroxymethyl- pyrazole hydrochloride.
the composition can include at least one inert additive relative to the compound of formula I, such as stabilizers, spreading agents, wetting agents, sticking agents, fillers, bactericides, fungicides, pesticides, or any combination thereof.
the combination can be in the form of a solution or dispersion with the carrier being inert relative to the compound of formula I, and can be liquid or powders.
the carrier can be water or a flowable powder.
microorganism is intended to include but is not limited to bacteria, fungi and yeasts, and is intended to include but is not limited to phytopathogens within these families.
the method and composition of the invention may be used to prevent attacks by at least one microorganism on plants, including but not limited to ornamental plants, fruit plants, vegetable plants and cereal crop plants and seeds thereof.
Ornamental plants can include orchids and roses; fruit plants can include orange trees and pear trees; vegetable plants can include cauliflower, tomatoes and onion plants.
Bactericidally or fungicidally effective amounts of the compound of formula can be alternatively applied to the bacteria, the fungi or the respective hosts, particularly hosts like plants, plant seeds, paper and the like, which are attacked by these microorganisms.
the bactericidal and fungicidal activities of the compounds of the invention are surprising in so far as N-methyl compounds of similar stability, for example, N-hydroxy-methylphthalimide, are not very effective with regard to their antimicrobial and preservative activity.
the compounds of this invention may be prepared by reacting either solid paraformaldehyde or an aqueous formaldehyde solution with a pyrazole derivative.
Preferred methods of preparation are given in Dvoretzky et al., Formaldehyde Condensation in the Pyrazole Series, 15 Journ. Org. Chem. 1285-8 (1952) and Huttel et al., Mannichsche Concept der Pyrazole, 85 Chemsiche Berichte 820-26 (1952), both hereby specifically incorporated by reference.
Another preferred method of preparation is given in European Patent application of Buck- man Laboratories International, Inc. filed concurrently herewith.
the antimicrobial activity of the compounds used in accordance with the invention extends to a variety of different microorganisms, including but not limited to bacteria such as Erwinia caratovora, Agrobacteria sp., corynebacteria, Xanthomonas sp., Pseudomonas sp., Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa, and including but not limited to fungi such as Pythium ultimum, Helminthosporium sativum, Rhizoctania solani, Fusarium oxysporum, Monilia fructicola, Peronospora parasitica andaltenaria solani.
bacteria such as Erwinia caratovora, Agrobacteria sp., corynebacteria, Xanthomonas sp., Pseudomonas sp., Escherichia
the preferred compounds of this invention include 3,5-dimethyl-1-hydroxymethylpyrazole, or the hydrochloride salt thereof, which generally exhibit relatively increased bactericidal and fungicidal activity under identical conditions over the 3,5-dimethyl-4-substituted-1-hydroxymethylpyrazoles in accordance with the invention.
the pyrazoles of this invention may be formulated and applied in bactericidal orfungicidal amounts, as the case may be, by conventional art methods.
the compounds of formula I are preferably used in a composition with one or more inert liquid or solid carriers or excipients such as powders, solutions and dispersions, most preferably in a spray with water or a flowable powder.
Compositions of these pyrazoles may also contain compatible stabilizers, spreading agents, wetting agents, sticking agents, fillers, other bactericides, other fungicides, pesticides and the like, and combinations thereof.
concentration of the compounds used in accordance with the invention which inhibits growth and proliferation of at least one microorganism, and thus provides the antimicrobial activity described herein, may be readily determined by one skilled in the art without extensive experimentation. Factors affecting concentration include but are not limited to weather conditions, the type of plant(s) and the type of microorganism(s) present.
An effective dosage may possibly be as low as about 2500 parts per million (ppm) (about 0.5% weight per volume water solution basis), will range from about 2500 ppm to about 30,000 ppm (about 3.0%), preferably in the range from about 15,000 (about 1.5%) ppm to about 25,000 ppm (about 2.5%).
One or more applications of the compound may be undertaken, as required, with factors affecting frequency of application including but not limited to weather conditions, the type of plant(s), and the type of microorganism(s) present.
the bactericidal effectiveness of these compounds was demonstrated in bacterial suspensions prepared by washing a culture of the desired bacteria from agar slant with sterile water into a vessel and further diluting the aqueous suspension to 250 ⁇ L with sterile water.
the test was conducted as follows:
the mycelial drop method was used to test fungicidal activity. This method measures the fungitoxicity of a compound in terms of its inhibition of fungus mycelial growth.
the general procedure was as follows: Each pyrazole to be tested was dissolved in acetone to a 100 ppm up to 15,000 ppm concentration. Equal volumes of these solutions were applied to the centers of each of three replicate paper discs inoculated with the desired fungus mycelium and placed on potato-dextrose agar medium.
the discs were incubated along with inoculated but untreated control discs at ambient temperatures until the control discs were filled with mycelial growth.
the fungicidal activity of the pyrazole was determined by comparing the radii of mycelial growth away from the edges of the treated and control discs. Prom this comparison a percent inhibition based on the relative mycelial growth areas was determined. The results of this comparative fungicidal test at two selected concentrations appear below in Table II.
the slide spore germination method was also used to test fungicidal activity. This method is described in the American Phytopathological Society Journal, Vol. 33, pages 627-632 (1943), and measures the fungitoxicity of compounds in terms of their percent inhibition of fungus spores.
the general procedure was as follows: Each pyrazole to be tested was dissolved in acetone to several concentrations between 50 ppm up to 15,000 ppm. These solutions were then pipetted into the wells of depression slides and allowed to dry. The wells were filled with a spore suspension of the specified test organism and incubated in a moist chamber overnight.
pyrazoles of this invention were tested by the mycelial drop method as described above in Example 2, except that these pyrazoles were dissolved in acetone to a concentration of 500 ppm.
a composition in accordance with the invention comprising a water solution containing 1.5 percent (about 15,000 ppm) on a weight by volume basis of a compound containing 98.0 percent on a weight by weight basis of 1-hydroxymethyl-3,5-dimethylpyrazole was prepared by dissolving 30 grams of the compound (technical grade) in 20 liters of water.
the cauliflower was sprayed with the aforementioned composition until liquid ran off the foliage. Three days later, the soft rot wounds were observed to be dried, an indication that the Erwinia bacterium was no longer active. The treated plants were observed to be recovered completely. Furthermore, no phytotoxicity was induced on the cauliflower plant by spraying this composition.
the degree of infection in the cauliflower by the Erwinia bacterium was recorded on the basis of the following key: The results of this test are summarized in the following Table IV:
a composition in accordance with the invention containing 5 percent on a weight by volume basis of the active compound in water as in Example 5 was prepared by dissolving 100 grams of the technical grade of the compound in 20 liters of water.
a cauliflowerfield infested with the fungus Peronospora parasitica was sprayed with the 1.5 percent composition as prepared in Example 5.
the Peronospora fungus attacks the foliage and cauliflower head producing sunken dark spots (small to larger than one inch), which make the agricultural product unfit for human consumption.
sunken dark spots small to larger than one inch
the disease incidence in the cauliflower was recorded on the basis of the following key:
a composition containing 1-hydroxymethyl-3,5-dimethylpyrazole was tested for controlling fungal and bacterial diseases interfering with cabbage seed germination.

Landscapes

Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Environmental Sciences (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
General Health & Medical Sciences (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pretreatment Of Seeds And Plants (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Immobilizing And Processing Of Enzymes And Microorganisms (AREA)

EP91306611A 1990-07-20 1991-07-19 Schutz gegen Mikroorganismen auf Pflanzen mit 1-Hydroxymethylpyrazolen Expired - Lifetime EP0467708B1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US555035		1990-07-13
US55503590A	1990-07-20	1990-07-20

Publications (3)

Publication Number	Publication Date
EP0467708A2 true EP0467708A2 (de)	1992-01-22
EP0467708A3 EP0467708A3 (en)	1992-08-19
EP0467708B1 EP0467708B1 (de)	1998-11-04

Family

ID=24215714

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP91306611A Expired - Lifetime EP0467708B1 (de)	1990-07-20	1991-07-19	Schutz gegen Mikroorganismen auf Pflanzen mit 1-Hydroxymethylpyrazolen

Country Status (15)

Country	Link
US (1)	US5225432A (de)
EP (1)	EP0467708B1 (de)
JP (1)	JP3076627B2 (de)
AT (1)	ATE172842T1 (de)
AU (1)	AU647496B2 (de)
BR (1)	BR9103159A (de)
CA (1)	CA2047415C (de)
DE (1)	DE69130439T2 (de)
DK (1)	DK0467708T3 (de)
ES (1)	ES2125863T3 (de)
FI (1)	FI102449B (de)
MX (1)	MX174310B (de)
NO (1)	NO180404C (de)
NZ (1)	NZ238917A (de)
ZA (1)	ZA915395B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997024031A1 (en) *	1995-12-29	1997-07-10	Buckman Laboratories International, Inc.	Synergistic antimicrobial compositions containing 1-hydroxymethylpyrazole and a preservative

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3577545A (en) *	1967-06-05	1971-05-04	Chevron Res	N-tetrahaloethylthio pyrazoles as bactericides and fungicides
US3409632A (en) *	1967-06-05	1968-11-05	Chevron Res	N-tetrahaloethylthio pyrazole pesticides
DE2835158A1 (de) *	1978-08-10	1980-02-21	Bayer Ag	Substituierte pyrazol-derivate sowie verfahren zu ihrer herstellung
US4801362A (en) *	1987-12-11	1989-01-31	Buckman Laboratories International, Inc.	Control of microorganisms in aqueous systems with 1-hydroxymethylpyrazoles
US4966908A (en) *	1988-03-21	1990-10-30	Ciba-Geigy Corporation	Isonicotinic acid amides for protecting plants against disease
JP2640617B2 (ja) *	1993-07-27	1997-08-13	クレハエラストマー株式会社	弾性リングの製造方法

1991
- 1991-07-10 NZ NZ238917A patent/NZ238917A/en not_active IP Right Cessation
- 1991-07-11 ZA ZA915395A patent/ZA915395B/xx unknown
- 1991-07-12 AU AU80422/91A patent/AU647496B2/en not_active Ceased
- 1991-07-18 FI FI913465A patent/FI102449B/fi active
- 1991-07-19 DK DK91306611T patent/DK0467708T3/da active
- 1991-07-19 ES ES91306611T patent/ES2125863T3/es not_active Expired - Lifetime
- 1991-07-19 BR BR919103159A patent/BR9103159A/pt not_active IP Right Cessation
- 1991-07-19 EP EP91306611A patent/EP0467708B1/de not_active Expired - Lifetime
- 1991-07-19 MX MX9100300A patent/MX174310B/es unknown
- 1991-07-19 NO NO912845A patent/NO180404C/no not_active IP Right Cessation
- 1991-07-19 JP JP03179861A patent/JP3076627B2/ja not_active Expired - Fee Related
- 1991-07-19 DE DE69130439T patent/DE69130439T2/de not_active Expired - Fee Related
- 1991-07-19 CA CA002047415A patent/CA2047415C/en not_active Expired - Fee Related
- 1991-07-19 AT AT91306611T patent/ATE172842T1/de not_active IP Right Cessation
- 1991-12-09 US US07/803,722 patent/US5225432A/en not_active Expired - Lifetime

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997024031A1 (en) *	1995-12-29	1997-07-10	Buckman Laboratories International, Inc.	Synergistic antimicrobial compositions containing 1-hydroxymethylpyrazole and a preservative
US5859040A (en) *	1995-12-29	1999-01-12	Buckman Laboratories International, Inc.	Synergistic antimicrobial compositions containing 1-hydroxymethylpyrazole and a preservative

Also Published As

Publication number	Publication date
JP3076627B2 (ja)	2000-08-14
EP0467708B1 (de)	1998-11-04
ATE172842T1 (de)	1998-11-15
FI913465A0 (fi)	1991-07-18
CA2047415A1 (en)	1992-01-21
FI913465L (fi)	1992-01-21
DE69130439T2 (de)	1999-04-08
ES2125863T3 (es)	1999-03-16
DK0467708T3 (da)	1999-07-19
ZA915395B (en)	1992-04-29
EP0467708A3 (en)	1992-08-19
NO912845D0 (no)	1991-07-19
NO912845L (no)	1992-01-21
BR9103159A (pt)	1992-05-05
US5225432A (en)	1993-07-06
NO180404B (no)	1997-01-06
MX174310B (es)	1994-05-04
AU8042291A (en)	1992-01-16
JPH04234302A (ja)	1992-08-24
AU647496B2 (en)	1994-03-24
NZ238917A (en)	1994-04-27
DE69130439D1 (de)	1998-12-10
CA2047415C (en)	1997-09-30
FI102449B1 (fi)	1998-12-15
NO180404C (no)	1997-04-16
FI102449B (fi)	1998-12-15

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